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BRENDA support

Ligand propionyl-CoA

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Basic Ligand Information

Molecular Structure
Picture of propionyl-CoA (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C24H40N7O17P3S
propionyl-CoA
QAQREVBBADEHPA-IEXPHMLFSA-N
Synonyms:
1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one, n-propanoyl-CoA, n-propionyl-CoA, propanoyl-CoA, propionyl-SCoA, propionyl CoA
Pathway Source
Pathways
MetaCyc
(S)-lactate fermentation to propanoate, acetate and hydrogen, (S)-propane-1,2-diol degradation, 2,4-dinitrotoluene degradation, 2-methyl-branched fatty acid beta-oxidation, 2-methylcitrate cycle I more


Show all pahtways known for Show all BRENDA pathways known for propionyl-CoA

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (35 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propanoyl-CoA + NADH + H+ = propanal + CoA + NAD+
show the reaction diagram
-
propanoyl-CoA + NADH + H+ = propanal + CoA + NAD+
show the reaction diagram
-
propionyl-CoA + oxaloacetate = (S)-methylmalonyl-CoA + pyruvate
show the reaction diagram
-
propionyl-CoA + L-carnitine = CoA + propionyl-carnitine
show the reaction diagram
-
propionyl-CoA + 10-deacetylbaccatin III = CoA + 10-deacetyl-10-propionylbaccatin III
show the reaction diagram
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3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl-CoA + propanoyl-CoA = CoA + 3alpha,7alpha,12alpha-trihydroxy-24-oxo-5beta-cholestanoyl-CoA
show the reaction diagram
-
propionyl-CoA + malonyl-[acyl-carrier protein] = 3-oxo-valeryl-[acyl-carrier protein] + CoA + CO2
show the reaction diagram
-
propanoyl-CoA + phosphate = CoA + propanoyl phosphate
show the reaction diagram
-
propanoyl-CoA + glyoxylate = 2-hydroxyglutarate + CoA
show the reaction diagram
-
propanoyl-CoA + succinate = propanoate + succinyl-CoA
show the reaction diagram
-
propionyl-CoA + H2O = CoA + propionate
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propanal + CoA + NAD+ = propanoyl-CoA + NADH + H+
show the reaction diagram
-
2-propenoyl-CoA + reduced electron transfer flavoprotein = propanoyl-CoA + electron transfer protein
show the reaction diagram
-
(S)-methylmalonyl-CoA + pyruvate = propanoyl-CoA + oxaloacetate
show the reaction diagram
-
2-methylacetoacetyl-CoA + CoA = acetyl-CoA + propionyl-CoA
show the reaction diagram
-
ATP + propionate + CoA = AMP + diphosphate + propionyl-CoA
show the reaction diagram
-
(S)-methylmalonyl-CoA + Na+[side 1] + H+[side 2] = propanoyl-CoA + CO2 + Na+[side 2]
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (142 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propanoyl-CoA + NADH + H+ = propanal + CoA + NAD+
show the reaction diagram
-
propanoyl-CoA + NADH + H+ = propanal + CoA + NAD+
show the reaction diagram
-
propionyl-SCoA + CoASH = propionyl-SCoA + CoASH
show the reaction diagram
-
propionyl-CoA + oxaloacetate = (S)-methylmalonyl-CoA + pyruvate
show the reaction diagram
-
propionyl-CoA + 17-O-deacetylvindoline = CoA + 17-O-deacetyl-17-O-propionylvindoline
show the reaction diagram
-
propionyl-CoA + 2-hydroxyamino-6-methyldipyrido[1,2-a: 3',2'-d]imidazole = CoA + N-propionyloxyamino-6-methyldipyrido[1,2-a: 3',2'-d]imidazole
show the reaction diagram
-
n-Propionyl-CoA + salutaridinol = ?
show the reaction diagram
-
propionyl-CoA + H2O = propionate + CoA
show the reaction diagram
-
3alpha,7alpha,12alpha-trihydroxy-5beta-cholanoyl-CoA + propanoyl-CoA = CoA + 3alpha,7alpha,12alpha-trihydroxy-24-oxo-5beta-cholestanoyl-CoA
show the reaction diagram
-
propionyl-CoA + L-2,4-diaminobutanoate = CoA + N4-propionyl-L-2,4-diaminobutanoate
show the reaction diagram
-
propionyl-CoA + p-nitrophenyl-beta-D-galactopyranoside = CoA + p-nitrophenyl 6-O-propionyl-beta-D-galactopyranoside
show the reaction diagram
-
n-propionyl-CoA + pseudotropine = CoA + O-n-propionylpseudotropine
show the reaction diagram
-
propanoyl-CoA + imidazole = CoA + N-propanoylimidazole
show the reaction diagram
-
propionyl-CoA + (S)-1-aminoethylphosphonic acid = CoA + ?
show the reaction diagram
-
n-propionyl-CoA + glycine = CoA + 2-amino-3-oxopentanoate
show the reaction diagram
-
propionyl-CoA + L-serine = CoA + O-propionyl-L-serine
show the reaction diagram
-
propionyl-CoA + L-homoserine = CoA + O-propionyl-L-homoserine
show the reaction diagram
-
propionyl-CoA + glycine = ?
show the reaction diagram
-
propionyl-CoA + [acyl-carrier protein] = CoA + propionyl-[acyl-carrier protein]
show the reaction diagram
-
propionyl-CoA + D-glucosamine 6-phosphate = CoA + N-propionyl-D-glucosamine 6-phosphate
show the reaction diagram
-
propionyl-CoA + L-arginine = N-[(4S)-4-amino-5-oxoheptyl]guanidine + CO2 + CoA
show the reaction diagram
-
propionyl-CoA + 5-aminosalicylate = CoA + N-propionyl-5-aminosalicylate
show the reaction diagram
-
propionyl-CoA + L-leucine = CoA + propionyl-L-leucine
show the reaction diagram
-
propionyl-CoA + alkyl-lyso-glycero-phosphocholine = CoA + 2-propionyl-1-alkyl-sn-glycero-3-phosphocholine
show the reaction diagram
-
propionyl-CoA + glycine = CoA + N-propionylglycine
show the reaction diagram
-
propionyl-CoA + phosphate = CoA + propionyl phosphate
show the reaction diagram
-
propionyl-CoA + cinnamyl alcohol = CoA + cinnamyl propionate
show the reaction diagram
-
acetyl-CoA + propionyl-CoA = CoA + 3-oxopentanoyl-CoA
show the reaction diagram
-
propionyl-CoA + 13-hydroxylupanine = CoA + 13-propionyloxylupanine
show the reaction diagram
-
glyoxylate + propionyl-CoA + H2O = 2-oxopentanedioic acid + CoA
show the reaction diagram
-
propionyl-CoA + citrate = propionate + (3S)-citryl-CoA
show the reaction diagram
-
propanoyl-CoA + succinate = propanoate + succinyl-CoA
show the reaction diagram
-
propionyl-CoA + malonate = malonyl-CoA + propanoate
show the reaction diagram
-
propionyl-CoA + H2O = CoA + propionate
show the reaction diagram
-
propionyl-CoA + H2O = propionate + CoA
show the reaction diagram
-
propionyl-CoA + H2O = CoA + propionate
show the reaction diagram
-
propionyl-CoA + H2O = CoA + propionate
show the reaction diagram
-
propionyl-CoA + H2O = ?
show the reaction diagram
-
ADP + phosphate + propionyl-CoA = ATP + propionate + CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (78 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-methyl-3-oxopropanoate + CoA + NAD+ = propanoyl-CoA + CO2 + NADH
show the reaction diagram
-
2-oxobutyrate + CoA + NADP+ = propionyl-CoA + CO2 + NADPH
show the reaction diagram
-
propionaldehyde + NAD+ = propanoyl-CoA + NADH
show the reaction diagram
-
propionyl-SCoA + CoASH = propionyl-SCoA + CoASH
show the reaction diagram
-
2-ketobutyrate + CoA + oxidized ferredoxin = propanoyl-CoA + CO2 + reduced ferredoxin
show the reaction diagram
-
(S)-methylmalonyl-CoA + pyruvate = propanoyl-CoA + oxaloacetate
show the reaction diagram
-
propionyl-L-carnitine + CoA = propionyl-CoA + L-carnitine
show the reaction diagram
-
CoA + 3-oxopentanoyl-CoA = acetyl-CoA + propanoyl-CoA
show the reaction diagram
-
CoA + propanoyl phosphate = propanoyl-CoA + phosphate
show the reaction diagram
-
2-oxobutyrate + CoA = propionyl-CoA + formate
show the reaction diagram
-
propionylcarnitine + CoASH = propionyl-CoA + L-(-)carnitine
show the reaction diagram
-
2-methylacetoacetyl-CoA + CoA = acetyl-CoA + propionyl-CoA
show the reaction diagram
-
glutaconyl-CoA + propionate = propanoyl-CoA + glutaconate
show the reaction diagram
-
acetyl-CoA + propionate = acetate + propanoyl-CoA
show the reaction diagram
-
propanoate + succinyl-CoA = propanoyl-CoA + succinate
show the reaction diagram
-
propionate + acetoacetyl-CoA = propionyl-CoA + acetoacetate
show the reaction diagram
-
methylmalonyl-CoA = propionyl-CoA + CO2
show the reaction diagram
-
methylmalonyl-CoA = propanoyl-CoA + CO2
show the reaction diagram
-
ATP + propanoate + CoA = AMP + diphosphate + propanoyl-CoA
show the reaction diagram
-
ATP + propionate + CoA = ADP + phosphate + propionyl-CoA
show the reaction diagram
-
propionate + ATP + coenzyme A = propionyl-CoA + AMP + diphosphate
show the reaction diagram
-
ATP + propionate + CoA = AMP + diphosphate + propionyl-CoA
show the reaction diagram
-
ATP + propionate + CoA = ADP + phosphate + propionyl-CoA
show the reaction diagram
-
ATP + propionate + CoA = ADP + phosphate + propionyl-CoA
show the reaction diagram
-
(S)-methylmalonyl-CoA + Na+[side 1] + H+[side 2] = propanoyl-CoA + CO2 + Na+[side 2]
show the reaction diagram
-

Enzyme Cofactor/Cosubstrate (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight activation at low concentrations, synergism with NADH plus NAD+
-

Inhibitor in Enzyme-catalyzed Reactions (28 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
weak
-
CPT I, inhibition is not affected by proteinase treatment
-
inhibition of both isozymes at 0.1 mM
-
competitive against acetyl-CoA
-
competitive to CoA
-
competitive inhibition
-
i.e. SID 7975595, a competitive, fast-on rate, fully reversible inhibitor of RmlC. Increases the Km for TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose. Cytotoxic SID 7975595 has an IC50 of approximately 0.075 mM in HAE cells
-
below 0.1 mM almost as effective as substrate as acetyl-CoA, inhibitory at higher concentrations
-
competitive with respect to 3-methylcrotonoyl-CoA
-

3D Structure of Enzyme-Ligand-Complex (PDB) (43 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (51 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.09
-
mutant NeuO + 36 hepta-nucleotide repeats
14.7
-
cosubstrate: (S)-1-aminoethylphosphonic acid, pH 7.5, 25°C
0.21
-
pH 7.6, 55°C
0.317
-
pH 6.0, 37°C
0.04
-
hydrolysis, absence of MgCl2, pH 7.4, 25°C
0.72
-
at pH 7.0 and 25°C
12
-
at 30°C
21
-
at pH 7.3 and 37°C
21
-
pH 7.3, 37°C, acetate-forming direction, with propionyl-CoA

KM Value (104 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
5
-
-
0.13
0.15
-
0.034
-
-
0.22
-
mutant NeuO + 36 hepta-nucleotide repeats
0.068
-
-
0.098
-
p-nitrophenyl-beta-D-galactopyranoside
0.07
-
cosubstrate: (S)-1-aminoethylphosphonic acid, pH 7.5, 25°C
0.08
-
-
0.263
-
-
0.13
-
pH 7.6, 37°C
0.128
-
-
0.3
-
at pH 7.4 and 30°C
0.0071
-
at pH 7.0 and 25°C
0.205
-
pH 7.0, 25°C, cosubstrate acetoacetate
1.9
-
pH 6.0, 30°C
0.005
0.012
estimated from rates at lower and higher substrate concentration
0.032
-
at pH 7.3 and 37°C
0.032
-
pH 7.3, 37°C, propionate-forming direction, with propionyl-CoA

Ki Value (9 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.3
-
inhibition of CO/acetyl-CoA exchange reaction
0.00049
-
-
0.71
-
-
0.005
-
pH 8.0
0.053
-
versus CoA
3
-
pH 6.0, 30°C
0.83
-
recombinant enzyme, pH 8.0, 30°C

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0002
-
pH 7.4, 25°C

References & Links

Links to other databases for propionyl-CoA

ChEBI
PubChem
ChEBI
PubChem